Leesburg Holiday Rentals

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Holiday Rentals in Leesburg

Waterfront Cottage on the Harris chain in Leesburg

9.8 out of 10, Exceptional, (83)
"excellent place, very peaceful, love the water"
Waterfront Cottage on the Harris chain in Leesburg

Siena at Bella Collina

3.5 star property
9.8 out of 10, Exceptional, (61)
"Great place to stay for group going to wedding venue. "
The price is AU$632
includes taxes & fees
24 Nov - 25 Nov
Siena at Bella Collina

Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart

10.0 out of 10, Exceptional, (10)
"House was immaculate and well stocked with everything we needed. Host was very responsive to questions both before and during stay. It was the perfect location for us to hop in the golf cart and head to Lake Sumter Landing. Would definitely stay here again. "
Sparkling! Walking distance to Sumter Landing,pools & more,or take our golf cart

Marilyn’s Romantic Getaway

10.0 out of 10, Exceptional, (54)
"This cottage was fabulous I would stay there forever if available "
Marilyn’s Romantic Getaway

Cozy Villages villa, 2 bed, 2 bath. Great Location

10.0 out of 10, Exceptional, (44)
"A good clean rental property with the added benefit of a four seater golf cart, as we were three adults a four seater was a must. The price was good as well. "
Cozy Villages villa, 2 bed, 2 bath. Great Location

BEAUTIFULLY Decorated 2/2 Sm Dog Friendly w/NEW GAS GOLF CART, BBQ & BICYCLES

9.6 out of 10, Exceptional, (11)
"This rental property was a great place to stay. Nicely located near activities."
BEAUTIFULLY Decorated 2/2 Sm Dog Friendly w/NEW GAS GOLF CART, BBQ & BICYCLES

BRAND NEW Dog Friendly 2/2 w. Golf Cart - Close to Activities, Shopping, Dining!

10.0 out of 10, Exceptional, (46)
"Would definitely stay there again"
BRAND NEW Dog Friendly 2/2 w. Golf Cart - Close to Activities, Shopping, Dining!

Pool, Golf course view home with a golf cart

10.0 out of 10, Exceptional, (31)
"We’ve been staying at the Villages for a number of years. The home was especially immaculate. Everything you could think of then some location location location was excellent.. We will be sure to return"
Pool, Golf course view home with a golf cart

Patio Villa in Duval Village - *** Gas Golf Cart INCLUDED ***

9.8 out of 10, Exceptional, (69)
"Good impression with all necessary equipments."
Patio Villa in Duval Village - *** Gas Golf Cart INCLUDED ***

Sunny Florida Escape w/ Pool Access, Patio & Grill

10.0 out of 10, Exceptional, (6)
"The place was clean, well appointed, and came with concise instructions and info from the owner. Excellent!"
Sunny Florida Escape w/ Pool Access, Patio & Grill

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart

10.0 out of 10, Exceptional, (80)
"Eve"
Fully Furnished Brand New Villa in Village of St. Catherine's with Cart

Unique Private Island 62 Acre Estate!

10.0 out of 10, Exceptional, (21)
"Great place with wonderful ownership and the most helpful staff. Definitely a place everyone should stay!!!"
Unique Private Island 62 Acre Estate!

New 3/2 Patio Villa, BEST VALUE, Golf Cart Included!

9.8 out of 10, Exceptional, (10)
"Lovely house in great location with everything you might need during your stay! Host was very proactive and accommodating with changes to our dates of stay due to the hurricane. Would definitely recommend. "
New 3/2 Patio Villa, BEST VALUE, Golf Cart Included!

Pet-Friendly Home w/ Lanai + Resort Amenities!

10.0 out of 10, Exceptional, (13)
"Great Location!"
Pet-Friendly Home w/ Lanai + Resort Amenities!

Get Cozy in this newly renovated home by The Villages!

10.0 out of 10, Exceptional, (9)
"Great place, plenty of beds for all of us to stay while visiting family in the nearby Villages. Easy to get to and instructions for accessing the property were straightforward. Host responded quickly to any questions we had. Would gladly stay again!"
Get Cozy in this newly renovated home by The Villages!

WOW .. ELEGANT Courtyard Villa with GOLF CART, Walk to Sumter Sq. 0.7 mi & pool

9.8 out of 10, Exceptional, (90)
"Loved proximity to Sumpter and the yard! Thanks for sharing. "
WOW .. ELEGANT Courtyard Villa with GOLF CART, Walk to Sumter Sq. 0.7 mi & pool

Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI

10.0 out of 10, Exceptional, (83)
"Enjoyed our stay in the villages"
Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI

Spacious home and country setting just minutes from The Villages.

8.8 out of 10, Excellent, (3)
"Master bath shower had black mold....self cleaned.....all else AOK"
Spacious home and country setting just minutes from The Villages.

Casa Linda, Stunning Country Experience, Powered By Nature & Natural Sunlight.

3.4 out of 10, (6)
"Never ended up staying at this property. When I reached out to the host for check-in information , I was told that tbe property is no longer available as a rental. I need a refund!!"
The price is AU$329
includes taxes & fees
28 Nov - 29 Nov
Casa Linda, Stunning Country Experience, Powered By Nature & Natural Sunlight.

Discover the Ultimate Comfort and Convenience in Country Club Hills!

Discover the Ultimate Comfort and Convenience in Country Club Hills!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Leesburg you may be interested in

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

2.0 star property
8.4 out of 10, Very good, (1002)
"The room was very clean and comfortable. I had a concerned about bedbugs, and i was told they have a pest control service to make sure rooms are clean and free of it. I will be staying at this place again. "
The price is AU$138
includes taxes & fees
24 Nov - 25 Nov
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

Best Western Plus Chain of Lakes Inn & Suites

2.5 star property
8.4 out of 10, Very good, (1019)
"Clean room, convenient location for the area. Have had better breakfast choices at other brand but it was adequate."
The price is AU$164
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Chain of Lakes Inn & Suites

TownePlace Suites by Marriott Leesburg

2.5 star property
9.2 out of 10, Wonderful, (231)
"Great, clean and friendly "
The price is AU$191
includes taxes & fees
1 Dec - 2 Dec
TownePlace Suites by Marriott Leesburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Leesburg?

Yes, there are holiday rentals close to the most popular sights in Leesburg, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and scenic lakeside in Leesburg. The live music and festivals are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Leesburg has to offer?

Beautiful view, The Villages- Golf Front Home, Heated Pool, Free Golf Cart, WIFI: This holiday home rental outside of Leesburg is located next to a golf course, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Leesburg?

Expedia has 34 holiday rentals for your stay in Leesburg.

What can I see and do in Leesburg?

Enjoy the outdoors at Venetian Gardens and Treasure Island, or simply take in cultural attractions like Paquette's Historical Farmall Museum and Paul P. Williams Auditorium. Lake Griffin and Lake Sumter Sports Complex and Recreation Area are other places to visit while you're in town.

What are holiday rentals like in Leesburg?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Leesburg. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip.